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Synthesis 2021; 53(09): 1629-1635
DOI: 10.1055/a-1334-6982
DOI: 10.1055/a-1334-6982
paper
Synthesis of the Common Monomeric Unit of Uroleuconaphins and Viridaphins via Hauser–Kraus Annulation
This work was supported by Grant-in-Aid for Scientific Research (C) (No. 19K05427 and No. 20K06955) from Japan Society for the Promotion of Science (JSPS).
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Abstract
A stereoselective synthesis of a pyranonaphthoquinone derivative found in aromatic polyketide-derived aphid pigments is reported herein. This approach features the anionic [4+2]-annulation of phthalides with a carbohydrate-derived optically active enone. Additional synthetic steps provide access to the monomer fragment of uroleuconaphins and viridaphins. The optimization for a facile preparation of phthalides bearing sulfonyl or cyano groups are also studied.
Key words
aphid pigment - polyketide - dimeric pyranonaphthoquinone - total synthesis - natural product - anionic annulation - Hauser–Kraus annulationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1334-6982.
- Supporting Information
Publikationsverlauf
Eingereicht: 27. November 2020
Angenommen nach Revision: 10. Dezember 2020
Accepted Manuscript online:
10. Dezember 2020
Artikel online veröffentlicht:
13. Januar 2021
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For reviews of aphid pigments, see:
For reviews of dimeric pyranonaphthoquinones, see:
For selected examples, see:
For selected examples, see: